Conditions | Yield |
---|---|
With perchloric acid In ethanol at 0℃; for 8h; pH=2; Reagent/catalyst; pH-value; Temperature; | 97.6% |
Conditions | Yield |
---|---|
With sulfuric acid In isopropyl alcohol at 0 - 12℃; for 4h; pH=2; Solvent; Temperature; Reagent/catalyst; pH-value; | 97.2% |
Conditions | Yield |
---|---|
With methanesulfonic acid In ethanol at 5 - 20℃; for 3h; pH=5; Solvent; pH-value; Temperature; Reagent/catalyst; | 96.6% |
toluene-4-sulfonic acid In methanol at 30℃; for 0.5h; |
Conditions | Yield |
---|---|
With dimethylphosphoric acid; boron trifluoride diethyl etherate at 3 - 20℃; Reagent/catalyst; Temperature; | 96.2% |
Conditions | Yield |
---|---|
Stage #1: dihydroartesiminin; trimethyl orthoformate In methanol at 20℃; for 0.25h; Stage #2: With acetyl chloride In methanol at 10 - 15℃; Stage #3: With sodium hydrogencarbonate In methanol; water at 0 - 5℃; for 2h; Product distribution / selectivity; | 74.67% |
Methyl (R)-3-hydroxybutyrate
dihydroartemisinin
A
9,10-dehydrodihydroartemisinin
B
artemether
C
C20H32O7
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature; | A n/a B n/a C 70% |
(S)-3-hydroxybutyric acid methyl ester
dihydroartemisinin
A
9,10-dehydrodihydroartemisinin
B
artemether
C
C20H32O7
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature; | A n/a B n/a C 56% |
Conditions | Yield |
---|---|
In benzene at 20℃; for 24h; Product distribution; Further Variations:; Reaction partners; Solvents; reaction times; | |
With hydrogenchloride In acetic acid methyl ester; water at 20 - 23℃; for 4.5h; Temperature; Concentration; Solvent; |
Conditions | Yield |
---|---|
Stage #1: 2-Methoxypropene; dihydroartesiminin In methanol at 20℃; for 0.25h; Stage #2: With methanesulfonyl chloride In methanol at 10 - 20℃; Stage #3: With sodium hydrogencarbonate In methanol at 20℃; for 2h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethoxy-propane; dihydroartesiminin In methanol at 20℃; for 0.25h; Stage #2: With chloro-trimethyl-silane In methanol at 10 - 20℃; Stage #3: With sodium hydrogencarbonate In methanol at 20℃; for 2h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
Stage #1: Trimethyl orthoacetate; dihydroartesiminin With sulfuric acid In methanol Stage #2: With sulfuric acid In methanol Stage #3: With sodium hydrogencarbonate In methanol; water Product distribution / selectivity; | |
With boron trifluoride diethyl etherate In methanol at 10 - 20℃; for 4h; | 98 g |
artemether
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In toluene at 25 - 30℃; for 12h; |
Conditions | Yield |
---|---|
Stage #1: dihydroartesiminin With dodecatungstophosphoric acid hydrate In dichloromethane at 20℃; for 0.0833333h; Stage #2: methanol In dichloromethane at 20℃; for 3h; optical yield given as %de; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / methanol 2.1: dodecatungstophosphoric acid hydrate / dichloromethane / 0.08 h / 20 °C 2.2: 3 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cellulose sulfuric acid; trimethyl orthoformate In tetrahydrofuran at -5 - 20℃; for 2.5h; | A n/a B n/a |
Conditions | Yield |
---|---|
With amberlyst-15 In 2-methyltetrahydrofuran at 20℃; for 4h; Kinetics; Reagent/catalyst; Temperature; Flow reactor; |
Conditions | Yield |
---|---|
With perchloric acid In dichloromethane at 30 - 38℃; for 0.166667h; Temperature; Large scale; | 756 g |
Conditions | Yield |
---|---|
Stage #1: C12H13O2(CH3)3(O)(OO) With methanol; sodium tetrahydroborate at -10 - -5℃; for 3h; Stage #2: Trimethyl orthoacetate With sulfuric acid; boron trifluoride diethyl etherate In methanol at 20℃; for 4h; pH=6 - 8; Catalytic behavior; Temperature; | 101.9 g |
artemether
Conditions | Yield |
---|---|
With zinc In acetic acid for 1h; Ambient temperature; | 72% |
artemether
Conditions | Yield |
---|---|
With iron(II) sulfate In water; acetonitrile at 37℃; | A 37% B 4% C 44% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; iron(II) sulfate In acetonitrile at 20℃; for 4h; Further byproducts given; | A 26% B 44% C 10% D 3.2% |
artemether
Conditions | Yield |
---|---|
Stage #1: artemether With titanium tetrachloride In dichloromethane at -78℃; for 0.0833333h; Metallation; Stage #2: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether In dichloromethane at -78℃; for 1h; Condensation; | 33% |
artemether
Conditions | Yield |
---|---|
With iron(II) chloride In acetonitrile for 0.0333333h; Ambient temperature; | A 23% B 16% C 32% |
artemether
1,4-diacetylbenzene bis(trimethylsilyl) enol ether
10-p-acetylphenylartemisinin dimer
Conditions | Yield |
---|---|
Stage #1: artemether With titanium tetrachloride In dichloromethane at -78℃; for 0.0833333h; Metallation; Stage #2: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether In dichloromethane at -78℃; for 1h; Condensation; | 26% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; iron(II) sulfate In acetonitrile at 20℃; for 4h; | 1.4% |
Mn(TPP)Cl
artemether
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium borohydride; cadmium(II) nitrate 1.) CH2Cl2, r.t., 1 h, 2.) CH2Cl2, DMF, 30 min; Yield given. Multistep reaction; |
artemether
A
β-2-deoxy-9-epidihydroartemisinin
B
(2S, 3R, 6S)-2-(3-oxobutyl)-3-methyl-6-<(R)2-propanal>-cyclohexanone
C
deoxydihydroqinghaosu
Conditions | Yield |
---|---|
With 1-Benzyl-1,4-dihydronicotinamide; lumiflavin In acetonitrile at 20℃; for 2.5h; pH=7.4; aq. phosphate buffer; Inert atmosphere; |
artemether
A
β-2-deoxy-9-epidihydroartemisinin
B
deoxydihydroqinghaosu
Conditions | Yield |
---|---|
With 1-Benzyl-1,4-dihydronicotinamide; riboflavin In acetonitrile at 20℃; for 3h; pH=7.4; aq. phosphate buffer; Inert atmosphere; | A 52 %Spectr. B 12 %Spectr. |
Conditions | Yield |
---|---|
With oxygen; methylene blue; ascorbic acid In acetonitrile at 20℃; for 24h; pH=7.4; aq. phosphate buffer; |
1. Introduction of Artemether
Artemether is one kind of white crystals or a white, crystalline powder. The chemical name of Artemether is (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin. The Product Categories of this chemical is Antimalarial. Artemether is toxic. It is flammable. It will produce Stimulate smoke when buring. So the storage environment should be ventilate, low-temperature and dry.
2. Properties of Artemether
Physical properties about Artemether are:
(1)Boiling Point: 358 °C; (2)Flash Point: 141 °C; (3)Density: 1.18 g/cm3; (4)Index of Refraction: 1.518; (5)Molar Refractivity: 76.54 cm3; (6)Molar Volume: 252.5 cm3; (7)Surface Tension: 39.9 dyne/cm; (8)XLogP3-AA: 3.1; (9)H-Bond Acceptor: 5; (10)Rotatable Bond Count: 1; (11)Exact Mass: 298.178024; (12)MonoIsotopic Mass: 298.178024; (13)Topological Polar Surface Area: 46.2; (14)Heavy Atom Count: 21.
3. Structure Descriptors of Artemether
(1) Canonical SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C;
(2) Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC)C;
(3) InChI: InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1;
(4) InChIKey: SXYIRMFQILZOAM-HVNFFKDJSA-N.
4. Toxicity of Artemether
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intramuscular | 263mg/kg (263mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 2, Pg. 138, 1981. |
mouse | LD50 | oral | 1gm/kg (1000mg/kg) | Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. D13, Pg. 280, 1992. | |
mouse | LD50 | subcutaneous | 390mg/kg (390mg/kg) | Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. D13, Pg. 280, 1992. |
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